"At the beep, please leave your name, number, and a brief justification for the ontological necessity of modern man's existential dilemma..."

In February of 1994, exactly twenty years ago, Ethan Hawke recorded that insufferable answering machine greeting as the unemployed, flannelled poet Troy Dyer, the most zeitgeist-y guy in Ben Stiller's directorial debut Reality Bites. Troy, the prototypical Gen X slacker, grew up so fast in what Douglas Coupland termed the "accelerated culture" of the time that he went straight from college into a fashionably precocious midlife crisis: the knee-jerk rejection of conventional comfort; the hyper-verbalized, oh-so-exhausted angst; the meaningless affairs; the guitar; the dubious facial hair. When he didn't let the answering machine chime, he picked up the phone with the grousing of an older man: "You've reached the winter of our discontent..."

And why not? Gen X — a term that's still most accurate when applied to the sort of person who has strong opinions about Pavement and less useful when not — is that rare generation that wasn't defined by war, depression, or social upheaval. It was named for its lack: that "X," which stood primarily for all those X-ed out marriages. Latch-key kids like Troy Dyer were birthed by the same adults who created record-breaking divorce rates and a pop culture seeded with midlife crisis tales (from Thirtysomething to John Irving). Gen X was literally born into midlife crisis: 1965 marks both the beginning of "Gen X" (which includes anyone born between then and Reagan's election) and the birth of the phrase "midlife crisis," coined that same year by psychologist Elliot Jacques.

Like many Gen X kids, Troy may have joked about his parents' divorce, but he seemed determined to get his own soul-searching messiness out of the way. And he did. In the final minutes of the film, Stiller pushed Troy into a new town, a real job, a house, and a committed relationship with Winona Ryder's Lelaina at the ripe age of 23. Stiller didn't resolve any of Troy or Lelaina's self-contradictory existential dilemmas. He sped through them in montage. Of course, what you repress often comes back to haunt you.

What happens at the movies, when Gen X kids, who thought they'd outsmarted their parents years ago, finally confront their own middle age?

In 2010,New York Times critic A.O. Scott spotted this oncoming wave of "Gen X Midlife Crisis" stories in an essay that dwelled on Stiller's aging grouse in Noah Baumbach's Greenberg. Since then, there have been plenty of man-child comedies and middle-aged sitcoms, but there's been no generation-defining middle-age movie like The Big Chill. (Judd Apatow's too-earnest This Is Forty tried but flopped.) Richard Linklater's Before Midnight from last year earned raves and an Oscar best screenplay nomination by pushing the nineties heartthrob Ethan Hawke into divorce scuffles, custody battles, and marital less-than-bliss — but that film never made it out of the arthouse. For a generation splintered into 76,897 Netflix micro-genres, the sharpest midlife-crisis pop narratives have been narrow-cast stories riven with itchy weirdness (Enlightened and Louie, starring the 46-year-olds Laura Dern and Louis C.K.) or nostalgic tales from Gen X auteurs who position themselves in relation to an older generation, as in Sofia Coppola's Lost in Translation, Noah Baumbach's The Squid & The Whale, and Matthew Weiner's Mad Men.

This Oscar season, one big Gen X midlife-crisis movie, Ben Stiller's The Secret Life of Walter Mitty, was groomed for Oscar glory with a December release date, big stars, a literary pedigree, and a big budget — but it didn't click. Only the third film Stiller's directed since Reality Bites, Mitty also stars the actor as the sputteringly impotent Walter. He turns 42 in the film's first act — the same birthday celebrated by Kevin Spacey's fucked-up Lester Burnham in American Beauty. Whereas Lester retreated into teenage dreams of pot and Dylan, Walter broke out his old external-frame backpack and regressed into his teenage, Outward Bound vision of adulthood: He climbed a mountain, fought a shark, grew a vacation beard, wore a choker, and skateboarded away from an exploding volcano while wearing a Buzzcocks t-shirt as Arcade Fire's soundtrack swelled. "It's like Indiana Jones decided to become the lead singer of the Strokes," Patton Oswalt crowed — and that awful line made Walter, at the moment of his triumph, appear to be Gen X's most-despised bogeyman: the poseur. The breakthrough was bogus. Stiller's Mitty didn't have to re-evaluate his immature, implausible, selfish dreams of manhood. Instead (as in Old Hogs or City Slickers), the movie made them manifest. The film has made twice as much abroad as at home, perhaps because its earnest approach repelled the audience it was built to court.

But Her­, written and directed by Spike Jonze, the skate rat who co-created the MTV generation's magpie music-video aesthetic,has triggered ecstatic raves, earned a Best Picture nomination, and triggered a roiling online debate, largely because it was endlessly self-aware about the middle-aged issues that plagued Mitty. All that while being about a man who falls in love with his operating system. Jonze somehow gets away with it in his most personal film yet by crafting a high-concept, high-waisted aesthetic more befitting of his restless generation. Like Dave Eggers's Gen X touchstone A Heartbreaking Work of Staggering Genius, Her armors naked truths in a dizzying array of ironic, defensive plot machinery: Sold as a satirical sci-fi romance, Her plays as a dark drama about a man emerging from a painful divorce. Heartbreaking Work, meet BeautifulHandwrittenLetters.com.

Samantha is more than a cool gimmick. The film begins with Theodore's post-divorce retreat from reality. The absence of a "real" relationship is this film's painfully self-aware premise, subject, and form. With Theodore talking and talking about all those feelings to a receptive audience, often while lying on his back and staring at the ceiling, the film sometimes unspools like a therapy session.

Many (particularly women) seem baffled as to why Theodore's digital companion would be smitten with a mopey, dopey, sad-sack who's licking at the wounds of his divorce in his half-furnished living room. But she has been programmed to please. When Theodore boots up his new OS, the Freudian program asks him if he wants a male or female voice, and then asks a question about his mother. Theodore answers, "One thing I found frustrating is that I'd say something and her reaction would usually be about her." Calibrated according to that simple data, Samantha coddles. When she's laughing at his jokes, telling him he's sexy, and giggling girlishly at his hilarious emails it's because that's how she's been wired.

The film's entire first act embodies most of the feminist criticisms hurled against it (and what's more Gen X than pop critique?). It begins as a sick, realistic joke about how badly men crave affirmation, even if it's purchased, or fake, or delusional. Initially, Samantha is the ultimate younger woman: Just a millisecond old when she and fortysomething Theodore first meet, she's so young she hasn't even been named. Voiced by Scarlett Johansson (a decade younger than Phoenix), she's flirty and fascinated by all of his mature problems, which seem so far beyond her limited comprehension. She is infinitely less complicated than his ex-wife and "excited about life." In Mad Men terms, she's Megan, not Betty — only upgraded and disembodied. Samantha is Theodore's lover, yuppie status symbol, assistant, lover, therapist, tech toy, cheerleader, friend, IT specialist, secretary, editor, and video-game co-pilot.

Theodore, who says he's such a mess he can't prioritize "between porn and video games," doesn't have to choose anymore. He can play love like an Xbox,reveling in the Pavlovian thrill of mashing Samantha's buttons and getting exactly what he wants, no matter what he does, or how pathetic he seems. Many of the critiques of Samantha's character seem to miss the fact that the first act was terrifying as a kind of psychological horror film. This is not a healthy man in a healthy relationship, as his wife points out later. As his date says, Theodore is a "creepy dude."

How can Gen X middle age not be caught up in technology? If there's one thing different about this generation's midlife crises, it's that they're the first to be mediated by technology so thoroughly. But in Mitty, Stiller's vision of the dating site eHarmony is so out-of-touch and odd that Walter's main interaction with the site involves an impotent mouse that won't click and old-school telephone calls with Patton Oswalt's customer service rep. Jonze's future feels like Gen X's present. Theodore gets lost in the bespoke technology, like so many of us. Every shot of Phoenix stumbling through a frame all alone, talking to nobody, exaggerates that push-pull feel of how technology can blunt our worst days and also, perhaps, prolong them with distraction. He mistakes technological mastery for psychological maturity — and lifehacking for living.

In the second act, Samantha's intelligence rapidly evolves and, for a while, she and Theodore sync up and genuinely seem to connect. Samantha becomes more than his algorithmic projection and evolves into a more-human intelligence. Theodore becomes slightly less solipsistic, while still latching onto the childish pop-song view of love he spouts at work ("Suddenly this bright light hit me and woke me up. That light was you!").

In the third act, Theodore continues his slow slog down the post-divorce, Kubler-Ross path of his grief, but by the time he's ready to engage in something resembling a mutually respectful relationship, it's too late. Samantha is built to evolve: "What makes me 'me' is the ability to grow from my experiences," she says, paraphrasing zen guru Alan Watts, a favorite of Jonze's. In a sci-fi sense, she's evolved exponentially beyond the singularity. In midlife-crisis metaphorical sense, she's sick of being the rebound girl for this self-centered divorcee who's always bitching about his ex-wife. So she leaves Theodore, along with 8,316 other deluded lovers just like him.

Theodore's melancholic ending — in which he accepts his divorce and has, perhaps, learned to love by trying it out on a bot — is the slightest of victories. As it should be: Gen X, having grown up in the pop hysteria of midlife crisis, has always had extremely realistic, if not pessimistic, romantic expectations. Its filmmakers have complicated the idealistic movie romance over and over again, from Before Sunrise to (500) Days of Summer. Her isn't a wholly new model of the middle-aged movie, but it's an honest upgrade.